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The first time my son wore a dress

As with any kid, my son's behavior doesn’t fit neatly into a stereotype.


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Posted on May 28, 2014   Updated on May 31, 2021, 6:00 am CDT


We were walking home from his daycare when I told my four-year-old boy that if he wanted a dress, we could get one. It was a hot day and I was carrying him because he was particularly sluggish that afternoon. His arms were squeezed tightly around my neck in a way that was both too warm and satisfyingly sweet.

My son was completely unamazed by my words, even though I had been preparing them all day while pretending to work. He would have been more amazed if I’d asked him if he wanted to go get some ice cream. He squeezed my neck even tighter and said, “I want a dress right now.”


It took some time to come to this. It had been months of us play-acting and him always being the girl, of him putting a towel on his hair and asking me to tie the towel into a ponytail, of him pretending to wear a dress and heels, of him asking me to call him a girl’s name.

At first, I tried to distract him from these interests. I’m not the most masculine of men and I don’t really fit the husband stereotype (I’m the one most likely to say: “Honey, let’s talk more about our feelings”), but I still had this unexpected instinct to steer him towards the Batman action figure instead of the Barbie dolls. Batman, Superman, and Spiderman —they were completely uninteresting to him. Wonder Woman was where it was at. Those beautiful bracelets. My boy was attracted to dolls, to fairies, to My Little Pony, to pink sandals, and to purple nail polish.

When we go by a pretty woman on the sidewalk, especially a woman in a dress and heels, he looks up at her so intently that he’ll sometimes stop walking or bump right into a telephone pole. (I thought that kind of thing only happened in cartoons.) After she goes by, he’ll point at her and he’ll say, “I like her,” with the word “like” rolling off his tongue for achingly long.

Sometimes, when I ask him to elaborate, he’ll tell me something he likes about her — usually her hair, sometimes her shoes or that red dress. But most of the time, he can’t articulate what it is. When a friend of mine was walking along with us one time, she commented that he must have a crush on the woman. But it’s not a crush. It goes deeper inside him than just crushing.


But first, let me back up.

Before he was born, my wife and I wanted a girl instead of a boy.

Wait. Let me back up some more.

I was single for most of the decade before meeting my wife. It wasn’t perfectly easy — I definitely had bouts of loneliness and depression — but I loved all that juicy time and space I had to write during those years. I had a day job to pay the bills and I went to the cafés and bars in the evenings and weekends to write fiction. I was very comfortable in this life. I even got pleasure from being that weird guy writing in the corner of the bar ignoring whatever sporting event or mating ritual was taking place around me. 

When I met my wife, we remained independent for quite a few years, living apart, careful not to step on each other’s solo projects. This is all part of another story, but for now, just know that I was used to being particularly greedy about my time. And then she got pregnant.

At the ultrasound, the young technician guy who was rubbing that gun-shaped device on my wife’s pregnant belly said, “Yep. That’s a boy all right.” I don’t think he was supposed to tell us before the doctor came in, but he was too excited when he figured it out. He tried to show us the penis on the screen, but it was all blur to me.

For my wife, the disappointment was short-lived — she already loved that baby inside of her, boy or girl. For me, it was messier. I walked around during the rest of the pregnancy thinking how much I didn’t want a boy, thinking of those bullying boys I once had to deal with as the most sensitive kid in the class. Were those mean little shits what typical boys were like to raise?

This period got dark for me. Which is why I not-so-creatively call it “our dark period,” especially when my wife and I are out with other potential parents. I like to think that I talk about this time to help open the conversation for anyone to talk about their own fears. Or maybe I just like to scare young, potential parents. Or maybe I just like to talk about it so I don’t forget. The darkness was more than just not wanting a boy, it was also a fear of having any kid at all. It was a terror of losing my personal space, my creative space, losing this whole life I had created for myself.

I started to feel a dread about my wife and this threatening boy in her belly. I wanted out of this situation so badly that I hoped for a miscarriage. (I hate to think about it now.) I wasn’t kind to my wife during this period either. Not in aggressive and violent ways, but in cold, quiet ways. When I came home from work, I wouldn’t look her in the eyes when talking about my day, as if I’d been cheating on her. I thought that the only reason I couldn’t leave her (them) was because I was a coward. I just didn’t have the courage to run off and be a deadbeat dad like other horrible men (whom I secretly admired).

I was scared of destroying this image of myself as a writer, novelist, or whatever I thought I was. And this dumb kid — even worse, this dumb boy! — was going to destroy it. Everything I was, was held in that fragile space, and it was about to fall apart. And I thought that would be the end of me.

During those months, I spent many nights drinking and roaming around through the supposedly bad parts of town. I fantasized about getting beaten up, being sent to jail. I wanted a one-way ticket to anywhere else.

We went through lots of therapy (individual and couples) to keep our marriage together during those months.

In a way, my fears were valid. I did lose a ton of time and space from my creative life. Those available hours disappeared. I just didn’t realize what would replace them. The value of this new thing. Which is not something you can ever know in advance, but I especially didn’t believe it would go that way. And I did find a way to keep writing and creating things, even if the number of hours per week changed dramatically.

When my son was born, the worrying disappeared. In an instant. He popped out and all I wanted was to take care of this kid. Boy or girl, tough or sensitive, it didn’t matter. He captured me and I was happy to be caught. It’s not that things got simple — raising a kid is a crazy mess of complicated—but at least this existential crisis fell away.


A few years later, when my son began doing these stereotypical girl things, I started thinking about my previous fear of having a child — in particular, the fear of having a boy. Some days, he even says, “Dada, I wish I was a girl instead of a boy.” Some days, he says it like he is about to cry and it is heartbreaking for me to hear it — just this idea of wanting to be something different.

Maybe it is worse because I know that feeling. In my 20s, there were many mornings when I woke up wishing I was not me. What if I caused this thing in him from all the crazy inside of me? What if I passed that sentiment on to him? Maybe I was to blame for how he was acting now. Maybe it was some defective chromosome I should’ve been tested for before deciding to have a kid. I walked around with a new ache about things not being quite right.

My first instinct was to fight for the boy he should want to be. He needs to be fully on board with this boy thing — even if I have to learn how to play stupid boy sports to make it happen. It was bizarre coming from this place of never feeling masculine to suddenly feeling like I needed to stand up for my gender.

But I didn’t know where to start. What did masculinity look like in the 21st century? I sure didn’t know.

One day my wife painted his fingernails and it bothered the hell out of me. “Get that shit off your fingers!” is what I initially thought. Though, fortunately, what I said was closer to: “Wow, I love those purple and pink nails.” I guess I thought that I shouldn’t let my wife do this to him. That she was pushing him to be this way and I needed to stop it. But I also saw how proud he was to show me those delicately painted fingernails.

It was a disorienting period. I carried a big pile of conflicting and contradictory feelings, for him, for her, and for me—with no way to think it through.


And then it got simple again. I’d love to have some profound insight or some wisdom about how this all changed, but the change was not an intellectual thing. It happened while playing with him on the floor one night, with ss both on our knees on the living room floor alongside some of his stuffed animals and plastic food objects. He was telling me that I needed to be Diego (from the cartoon, Go, Diego, Go!) so that he could be Diego’s sister, Alicia, and he had a bandana resting on his head to prove he was a girl. He handed me one of his stuffed cats. “This is our cousin, Dora,” he told me. “Now let’s go rescue that pretend pizza over there who has to poop real bad.”

Nothing particularly profound about a pooping pretend pizza, but it was just the particularness of these scenes we were reenacting each night. And his joy in playing out these stories. It was a privilege to watch him explore the world.

Who the hell was I to tell him another way? Blame stopped making sense. What is blamable here? This is being alive.


As with any kid, his behavior doesn’t fit neatly into a stereotype.

One time we got him a set of snap-together jewelry — a big jug of beads—because he seemed to be fascinated with jewelry. On the first day, he actually did focus on making jewelry—necklaces, bracelets, anklets, and rings. But then he decided the string of beads he had created looked more like eels and squids and octopi and other sea creatures. He lost all interest in the jewelry part of things.

For the next month, he spent about two hours a day playing on the rug with those sea creatures. There’s a zebra eel, a tiger eel, a blue squid, a baby octopus, and an electric butterfly eel. There is also a troublemaking scuba diver who always bothers the sea creatures. My boy makes me play the role of the scuba diver. I sometimes try to have the scuba diver learn from his mistakes and become nice, but my boy wants the troublemaker to keep causing trouble. I don’t know why.

All this pretend troublemaking causes me to think about my shy boy as he gets older and who might be the real troublemakers in his life. Will he find a group of sensitive kids to play with? Or will he be disconnected from the others? What will they think of the pink butterfly wings he got for Christmas? (Or was it Hanukkah?)


My wife and I are working through this experience in slightly different ways, and fortunately, our different ways seem to support each other. While she is reading more books about families in similar situations, I spend more time on the floor with him, play-acting however he wants to play.

One dad told me that his son was into pink until the second grade and now he’s the most boyish boy of all his friends. Everything changes after kindergarten. Other people explain that the way transgender people are being treated is getting better and better. That the surgery for converting a penis into a vagina is a lot easier than the other way around. There are gay support groups that are available. There are good books on the subject.

We get lots of feedback and it is mostly supportive and full of good intentions. We’re clearly living in a different time and place than when I grew up in Atlanta in the 1970s. I appreciate all this feedback and support.

But my instinct at this point — even though it is counter to how I normally, obsessively deal with issues—is not to dwell on how ten-years-from-now might go. Now is the time to linger on the simple joy of witnessing a kid experiment with who they want to be — untethered to what it means. Or what it doesn’t mean. Fuck all of this projecting and anticipating and categorizing. Just be here right now.

I’m not saying I know the right way to do this stuff. I totally don’t. Similar to my writing life, I have no idea what I am doing when I’m doing it. But when I’m with my boy and I let him go in his own direction without pushing him to go faster or slower, it feels right to me.

The afternoon I offered to get him a dress, he didn’t even want to go get ice cream like we usually did after daycare. We went straight to Goodwill.

There were other girls and moms in the girls’ section, and so I tried to stall my boy by looking at some of the half-broken toys that we normally love to explore, but he pulled me to the dress aisle like he had been shopping there a thousand times before. He is normally very shy in front of strangers, but he walked with authority next to the other kids and parents in search of a beautiful dress. He picked two pink dresses with flowers on them, one skimpy dress that seemed inappropriate even for a girl, and a white one that seemed only fit for a wedding. “Dada,” he said as he handed the white one to me. “I love this one the most.”

Another girl plucked at her mom’s skirt and when the mom leaned over, the girl said, “Why is that boy looking at girl things?” If my boy heard this question, he didn’t seem to react. The mother dodged the question by showing her daughter another dress. But the question made me want to squeeze my boy tighter. I picked him up to give him a better view of all the dresses on the two long racks.

Once we got home with the dresses, he took off his shirt and shorts right away. His mama — my wife — wasn’t home, so together my boy and I stumbled our way through the art of putting on a fancy, fluffy white dress. (Over the head? Do you step into it? Where does this string thingy tie?) I zipped him up in his first dress.

He had this smile on his face that was far bigger than ice cream. He took a few steps towards the center of our living room, in a way that seemed both more awkward and more graceful than usual. He inhaled one deep breath and then spun in a circle. We both watched his dress float out around him and then come back to rest.

Yuvi Zalkow is a writer, shame-ridden schmo, maker of lowbrow videos on creativity, and a half-assed podcaster. His novel is reluctantly available on Amazon. This piece was originally featured on Medium and reposted with permission.

Photo via allthecolor/Flickr (CC BY 2.0)

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*First Published: May 28, 2014, 8:30 am CDT